A Friendship Evolves, Thanks to An Unusual Date — With Grandpa

“I remember seeing her out of the corner of my eye, how she brought people into the conversation and how all the people surrounding her were laughing and having a good time,” he said. “I was thinking, Who placed me here and how can I get over there?”

For Mr. Ng, 30, wondering how to maneuver his way from a bad predicament into a better one felt familiar. Born in Toronto, he was raised as an only child by his mother, Mona Kwong, a factory seamstress who immigrated from Hong Kong to Canada in 1979 hoping to escape poverty. When he was 13, his parents divorced. His father, who also immigrated from Hong Kong, had been an infrequent presence at home, working at restaurants and casinos hours outside the city and returning only sporadically. “He kind of flowed in and out of my life, but mostly out,” he said.

Ms. Kwong, he said, “taught me everything I know.” Lesson No. 1 was to work hard. In 2005, shortly after his parents split, Ms. Kwong was laid off from her seamstress job. To help pay the bills, Mr. Ng cleaned houses with her on weekends. His domain was tubs and floors. “She did all the above-the-waist work, because bending over isn’t easy after you’ve spent a lifetime hunched over a sewing machine,” he said. Academic hard work and extracurricular hustle earned him full financial aid at Harvard.

Ms. Chen’s parents, James Chen and Wendy Pan, also immigrated to Canada, but from Beijing, where she was born and lived until the family left for Toronto in the late 1990s. Her maternal grandparents, who raised her while her parents worked long hours as producers on film and TV sets, came with them. Ms. Chen’s younger sister, Harriet, was born in Toronto. Three years later, the family settled in Vancouver. Better educational opportunities had brought them to Canada.

Ms. Chen is now 30. When she left for college, she was unsure about a career path. She had a triple major in business administration, economics and rhetoric, earning two bachelor’s degrees in 2013 while working part-time jobs to pay her tuition. She wasn’t done exploring her professional options when she signed on with Goldman Sachs in 2012. In 2015, she earned a law degree from the Chinese University of Hong Kong. A year later, she helped form the San Francisco venture capital firm IOVC, where she is still a general partner.